
Today, Rob flies solo to talk about 7 different things that he has learned in his 20 years of entrepreneurship. He also offers some feedback about what he is seeing in the startup communities today, advice on how to deal with competition, marketing tips, and how to build a team of developers.
The finer points of the episode:
- 2:35 – Be careful about over-generalizing from one win
- 3:33 – The three things you need in order to succeed in building a startup
- 8:10 – How to handle feedback you get on your product
- 12:48 – Rob’s personal experience and opinion on dealing with competition in the startup space
- 15:35 – Why word-of-mouth is not the right answer for where your leads are coming from
- 18:40 – The real reason why some startups are “transparent”
- 21:05 – Advice on how to build a team of developers
Items mentioned in this episode:
I think it’s more substantive and perhaps will reach more people in a deep fashion than posting it into Twitter. Today’s episode is going to be walking through seven different, I would almost call them advice but it’s more like these are things that I’ve learned in my 20 years of entrepreneurship and some things that are going on in the world today that I feel like I have commentary on.
When I say in the world, I don’t mean COVID-19. I mean more in our startup communities. I’m going to be talking about advice and feedback, a little bit about how to give a little bit, a little bit about taking it, and we’re going to be talking about competition and some specific experiences I’ve had around it. Talk a little bit about some marketing stuff and it’s not going to be high-level, this is how you market. It’s just some specific advice and mistakes. I think antipatterns in ways that I think people have been thinking about marketing as well as managing developers.
This all revolves around sometimes just one, but often it’s 5, 10, 20 conversations that I’ve had with colleagues, founders, or aspiring founders. When I start hearing the same thing over and over and I realize that I’m thinking about this in a different way than perhaps the early stage founder or just someone who hasn’t been in our space for a long time. I just like to bring these things up and talk them through.
One thing I want to say before I start is that it’s such a trip. Probably once a month I get an email that says, “I’ve been listening to your podcast for years and I had bought Start Small, Stay Small years ago. I had no idea that you were the same Rob.” Every couple of months, I’m going to say that I wrote Start Small, Stay Small. If you’ve read the book, thanks. I appreciate it, but just to clear the air so that you know that I’m one the same. I wanted to do that.
Let’s dive in. I have three things that I wanted to say about advice and feedback. The first one is something that I think has always happened, but it definitely has gotten more and more prevalent in the startup space. The more people that are just online and doing social stuff trying to build personal brands. I just want to ask if you are a founder who has had some modicum of success, please be really careful about overgeneralizing from one win.
I think of it the first time you launch a product and you have some success, suddenly you feel like you know exactly how to launch a product and that your experience applies to every product everywhere for all eternity. I’ve seen folks grow an app to 10,000, 30,000, 50,000 a month with no employees and they typically admit that they got pretty lucky. They found a niche that happened to grow, they rode a wave, or maybe they didn’t. Maybe they really just worked hard and it took them five, six, seven years to get there.
But then, going out and giving advice on this is how to start a startup and this is how everyone should do it is really dangerous. I had this mental model and I brought it up in the podcast in the past about the three things that you need to succeed in (let’s say) building a startup. One is hard work, the second is luck, and the third is skill.
You might have these in varying degrees. If you have tremendous skill in marketing, or tremendous skill in building an audience or building a network, or tremendous skill on choosing niches and building a great product, you may need less luck and I personally always think you should put hard work in because that’s the one you control the easiest in the short term is to work hard. I don’t mean 90-hour weeks, of course. If you listen to this podcast, you know that my entire entrepreneurial career, I’ve worked 40 hours a week or less except for some very short stints where I did work 60 hours a week for 6 weeks at a time, 8 weeks at a time to get some hard stuff done.
Hard work and focus (I think) is table stakes in my opinion, although if you are really lucky, I do know a founder who happened to be at the right place at the right time and just stumbled into a hobby, became something that was really popular. He got really lucky and sold the company for tens of millions of dollars. He didn’t actually work that hard. Self admittedly, he never really worked that hard but he did have the skill to build a team and he did really get lucky in the right place at the right time so it’s totally possible.
Then of course, there are folks who don’t get lucky at all. They just put tons of hard work and they build skills, and it takes them five or ten years to get where someone who got lucky maybe would have gotten to in one year. Those three things I think make up the building blocks, but to build a SaaS app or any company to $3000, $4000, $5000, $6000 is hard. Typically, you need to put in some hard work. Typically, you probably need a little bit of luck although not at that scale. I do think that to get to tens of millions or hundreds of millions, that you do need all these things to fall into place.
Oftentimes, after your first one, you just don’t know. You don’t know what made it work. You think you do, but after your second one, your third one, your fourth one, you start to see the patterns. I’ve grown seven businesses to at least six figures in revenue. Seven six-figured businesses I’ve created in the past of about 15 years. Actually, some of those weren’t six; they were at least six. There are few that are seven figures. Seven six- and seven-figured businesses is probably a better way to put it.
After the first one, I really did think that I’d do it all and it’s such a natural thing to want to go out and tell everyone about. When I did the second one, I realized nope. The things that I thought made it successful, some of them were right but about half of them were wrong, and when I go back and read writings that I did 10 years ago, it’s a little painful for me. I think most folks are not doing this intentionally. I think it’s a natural human desire to want to teach and I think it’s a natural human desire to want to talk about how you have the right answers.
Just consider this, most people giving advice are doing it to build a personal brand so they can sell you a book, or a course, or they’re even some investors who do that, and a lot of Silicon Valley folks like the venture capitalist would blog in order to get followers and then people will say they know what they’re doing. But really consider a question that I often ask myself when I see a new expert or a new name come on the scene. I typically ask myself have they done it at least twice? Obviously there are exemptions.
Jeff Bezos has not built two Amazons. The Collison brothers, actually I think they did have a startup before Stripe that was successful. Most founders I know really who know their stuff, they have done multiple. I look at Eaton Shaw, Jason Cohen, David Cancel, Dan Martell, people who have done it two, three, four, five times and there’s definitely a learned experience and definitely a different communication of their learnings as they get further along.
That’s the big question I ask myself. If someone is giving advice, I think, have they done it at least twice or three times that they can start seeing patterns. I also ask, are they giving advice on something that they really are expert in? Because again if you grow an app to $30,000 a month then you’re working on your own, that is so different than building a team, building a startup, and knowing how to build a team culture, knowing how to hire people, knowing how to cross a million dollars in ARR, knowing how to cross $2, $3, $4 million. It becomes such a different experience.
As I’ve watched founders who I’ve invested in or I’ve worked with or just known through MicroConf in this podcast. Each step you’re learning a lot and overtime I think that you’re really building that corpus and that wisdom so to speak so that you can share with others. I’ll stop there on the advice and I want to switch to this topic of feedback.
What I mean here is if you’re building a product, you’re trying to build something that people want, maybe you do have product/market fit, and things are growing. There’s always going to be someone who wants to give you feedback about your product, who doesn’t tend to know what they’re talking about but thinks they do. It’s often hard to tell. So, the thing that I have started doing because when we were growing Drip and frankly every business I’ve ever grown has this whether it’s a MicroConf, TinySeed, Drip, HitTail, or stuff that I grew before, someone wants to give you feedback.
In the early days when someone gave me feedback, I thought they must be an expert because I don’t give feedback to someone unless I feel like I really know what I’m talking about. Other people don’t necessarily have that bar. I would get an email when we were running Drip and we’re literally doing millions of dollars in revenue. Someone would say you really need to change this font color, change this button, or this tab in the interface. Just these really small things that are nitpicks and frankly are not going to change the business. They’re not going to change the business. The UX was really good and really solid. Could you find one pixel out of place? Of course you could. Does that change the business? Should we be focused on that?
It comes from people who I think are not entrepreneurs. They’re not founders. They’re not thinking about the business. They’re thinking about their particular expertise. That’s where it has gotten to a point where I really need someone to have some type of credentials before I listen to them and I don’t mean academic credentials, but when someone emails me out of the blue, if it’s Eaton Shaw, Ruben Gomez, Brennan Dunn, or Jordan Gal in the email and saying, “Hey, there’s something in your product I think you should fix,” I’m going to listen to it because they’re a founder. They are product-focused people who know how to build a good product and their feedback is very likely coming from a place of I’m trying to help you build a better product versus feedback coming from someone I don’t know and when I go to look at them, either they are not a UX designer at all and they just have an opinion or they are a developer and designer and they’re trying to sell me their services.
I just don’t know their motivation and frankly making changes that random people on the internet suggest about your writing, your product, your podcast, your blog, or your conference, it’s dangerous. Now taking it in aggregate, of course, is great. If you fear the same thing from all the people especially if you have thousands of customers, when you start hearing the same thing you have to look for patterns, yes you should do that. I’m not saying don’t listen to anyone. I’m saying be wary of the individual who feels like they are so confident in their advice, but how do you know if they know anything? And oftentimes they don’t.
This is different than someone coming in your app and saying, “Hey, I’m confused by this. I’m confused by this onboarding. I don’t know what to do here.” That’s bad. You don’t want people to be confused. It’s different than someone sending you a screencast and saying, “You really need to change this,” because it’s always like that’s your opinion. That’s your opinion and one person has said this and since I have 3000 customers, I’m going to go with my opinion on this one and not chase down a rabbit hole. That’s number two. That’s be wary of product feedback from people without credentials.
Third thing is something that Sarah Hatter said. Sarah Hatter runs CoSupport and she said on a MicroConf talk once and it resonated with me, was years ago, probably five or six years ago now, and keeping on the topic of advice and feedback, this is the last piece of this. She said, “Don’t take business advice from people who have crappy personal lives.” Let that sink in. A lot of people who give business advice have crappy personal lives. Oftentimes you don’t know, but if you do know, it’s a really interesting thing to think about how someone treats people and I’ve added this to the end.
“Don’t take business advice from people who have crappy personal lives,” and my addition is, “or who treat people in a way you don’t want to treat people.” The reason I’ve added that is because from what I’ve seen, you can be successful in business and treat people right or you can be successful in business and treat people like […].
If you don’t want to do the latter, then don’t take advice from people who do because I do think that it’s a contributing factor to their success. If you try to replicate their success with their advice, but you treat people right, you treat them fairly and you’re nice to them, I think there’s just a disconnect there. I’m not sure that advice is going to translate into what you think it’s going to do.
Let’s move on from advice and feedback to talk about competition. This is an interesting one. Again, this is one that has happened to me several times. I think three maybe more and it’s happened over the course of 15 years. I’ve been an entrepreneur for 20 although I was a consultant early on and really started building products 2003, 2004 and started. I think about 15-17 years is really my entrepreneurial career, but I’ve had three people say almost this exact sentence to me over the course of this time and I want you to hear it.
The sentence is, “There’s plenty of room in the market for all of us.” The first time I heard it, it was from someone who had essentially seen that I was having success in a space and proceeded to copy what I was doing in a way that was really obviously a copy. As we talked about it, the person said, “There’s plenty of market for all of us,” with a smile and a pat on the back because they didn’t want to make an enemy.
The first time I was like, “Oh yeah. No, that’s a really good point,” then I watched him replicate pieces of our positioning, a bunch of features, start to try to take our customers, and just on and on. The second time I heard it, I knew what it was. It was years later and I knew exactly it was someone trying not to make me mad and trying to be friendly with a competitor but that they were going to screw me again. They’re going to backstab me, but I didn’t say anything. The third time I called someone on it and I said, “I’m not sure that that’s the case,” and it really put this person on their heels because they didn’t expect that. But it’s just a fascinating sentiment.
I do believe that markets are big and the free market is fine, but don’t sit there and look me in the eye and tell me that we’re buds, that we’re friends, right before you stab me in the back. If you feel like you have this conversation and someone ever tells you, “Hey, there’s plenty of market for both of us,” just expect them to start drafting off you if they’re not already. What will be interesting is that you’ll be able to tell their next three moves by looking at the last three moves that you made. It becomes painfully, painfully obvious with folks like this who are copying you.
I’m not saying don’t worry about competition. I do think that you should focus on your customers and your audience, but I do think that competition, especially people like this who try to act like that they’re not competing with you but they are effectively ripping off what you’re doing, sometimes even the same naming, I do think it’s something that can be upsetting, to be honest. Frankly, when I talk to people who do have competition who are basically copying them—you’re the innovator, you spend time to do it, you prove it out, and then someone just starts copying it piece by piece—it’s frustrating on a personal level.
There’s something about it as a maker having someone replicate it and typically they claim that it’s their own and claim that they came up with it. That’s the frustrating part. Just be wary of that when you’re in a space and someone tells you that there’s plenty of market for all of us.
Next, I want to talk a little bit about marketing. I have two thoughts here. I’ve heard entrepreneurs who launch a business, business growing relatively well, and when I ask them where your leads or where you’re new customers are coming from, they say word-of-mouth. When I dig into that, the real answer is I don’t know where they’re coming from. So if you don’t know, don’t say word-of-mouth. Say you don’t know or find out because I think it’s really dangerous not to know where your customers are coming from.
I bought a business at one point where the founder told me that customers come from word-of-mouth. I said, “Why is that?” and she said, “It keeps going up to the right. It’s growing slowly,” but in Google it just says direct traffic and it turns out it’s not word-of-mouth. There were a number of factors. I’m going to point to a number of things that would be really hard to track.
You can go on podcast and mention the URL. You can talk from the stage. Someone could read about it in a book. They could read about it in a newspaper or magazine. They can have their referral being cleared out when they click through. They can be on a different device than when they originally heard about it. It could be a returning visit. There are just all these things that can lead to you not knowing where they’re coming from and you’re not going to be able to attribute 100%. You can’t do it.
But having an idea and frankly asking customers tends to be the best way. Asking where they first heard about you or where they heard about you right before they signed up for first touch and last touch attribution, and then of course looking at Google Analytics or whatever analytics you use, these are all good approaches. But the right answer to where my customers are coming from is almost never word-of-mouth.
Word-of-mouth is a component. I remember with Drip, word-of-mouth as far as we could measure it was 15%, 20%, 25% depending on how you measure it. Word-of-mouth is when someone else mentions me on a podcast or is that podcast marketing, it’d be that kind of stuff. But it was somewhere in the teens to the twenties of growth and that’s great.
Once you get to the seven figures of revenue, you build this thing that Jason Lemkin calls a mini brand, were not a brand like Coca-Cola or Chevrolet, but you are a small brand in a small niche and the conversation goes from marketing automation to Infusionsoft and Ontraport. When we started Drip, that’s what it was. Infusionsoft and Ontraport, and I wanted to be the third. I wanted it to be Infusionsoft, Ontraport, and Drip. Then quickly, Ontraport went on its way out it seemed then it was Infusionsoft, ActiveCampaign, and Drip, and those were the three.
We built this mini brand and yes, did we have word-of-mouth? Absolutely. Did we have a mini brand? Absolutely. But I knew that 30% of our new users came from integrations. I knew that X% came from organic search traffic. I knew that X% come from the podcasts that I was on. You can always pinpoint it but while you can build good word-of-mouth, it’s often less than you think it is. Just be wary.
If you don’t know where your customers are coming from, that’s something you’ll see me push my table on often. Where they’re coming from, how you can find more of them, because if you don’t know where they’re coming from, it’s just people referring to one another, your growth will always be capped. It will be capped at the rate that people will tell one another about them. This is different from affiliate marketing. I’m not going down that whole thing. I don’t consider that word-of-mouth because it tends to be very intentional when that works.
The second thing about marketing and then I’ll move on to managing developers. My second thought here is (and this may be obvious to you) to some folks whom I’ve talked to, it’s not, so I’ll just say it and move on. It’s not that big of a deal. Transparency in the startup space is mostly about marketing. Most transparency, I’d say 90% maybe 95%, is just spreading the word so that people will talk about them and that’s okay. Marketing is fine, but I don’t have a problem with marketing. I have a problem with disingenuous marketing in all honesty.
When a big name, huge affiliate marketer, blogger, podcaster that we all know always says yes, I have affiliate commissions but doesn’t talk about how most of the products that he promotes, he gets shares in the company. He has an ownership stake in the company, but you never hear him disclose that. That to me is disingenuous and I don’t like that kind of stuff.
I feel the same way about transparency and I don’t know that people realize that again, I would say 9 out of 10, or 19 out of 20 folks doing transparency are doing it to spread the word for marketing or to brag. I think there’s a lot of bragging about how much money I made, look at me, or frankly to get attention for a personal brand so they can sell you something like a course.
Again, I don’t think this is bad on its own. Just think about this the next time you see a company being transparent with all the good things that happen to them. It can be a range of things. It’s whether having all your revenue dashboard public or whether it’s publishing all your salaries or your internal thought processes or income, whatever. There’s a bunch of ways to be transparent. You just really think about why this person is doing it. Are they doing it to help you or are they doing it to draw attention to themselves?
As savvy consumers of a lot of things in 2020, I do think we need to be aware of whose advertising to us, whose marketing to us, what the messages are, and what the thoughts are behind it. Whether it’s Apple putting a billboard up or whether it’s a commercial, you got to teach your kids how to interpret commercials and say, “Wow, the toys aren’t actually going to be that fun. It looks fun because the kids on there are making it look fun but really once you get it home, it’s going to be kind of boring.” Same thing with transparency. Just know the thought process behind it and be aware of that.
Again, I’m not saying no one should be transparent. I’m not saying it’s a terrible thing and I’m not saying that marketing is bad. To be really clear, just know what’s going on behind a lot of the transparency that you see.
Last topic for today, it’s on managing developers and this one comes from I think only two conversations maybe three that I’ve had during my career and it’s typically what it’s always been when I worked at a larger organization. My advice is don’t try to quantify software development. Software development is a craft. Software development is not manufacturing.
The difference is building really good software, you need crafts people and you can’t do this by building an assembly line. You can build […] software by building an assembly line. You can build a car on a manufacturing line, but it’s much harder to build an amazingly intricate piece of art or a piece of furniture on an assembly line. That takes a craftsperson. There’s just a certain element of creativity and craft that you need and software development can be either.
It can be manufacturing, but good software development is a craft and what I’ve seen manufacturing lines at big companies of 20, 30, 40 developers and they want to quantify stuff like lines of code written, bugs fixed, that’s when you go down this line of (a) building crappy software, and (b) all your good developers are going to leave.
This really comes up when I’m talking to someone who has never written code or who has actually just wasn’t a developer. They were managers and they could quantify at a high level the support team, it’s ticket resolved and time to answer the ticket and the happiness of the customer. They can look at sales and they can say leads talk to, close time, and how much money they brought in. Then they will look at the development and they will say I want to do the same thing there.
I always told them that doesn’t work. There’s no number. There’s no set of numbers. No, we can look at some OKRs and KPIs, two acronyms that I despise and hopefully I never have to use them at another company again, but we can put some things down and we’re shipping features. What’s our velocity? There are ways to quantify this.
There are agile development and sprints, and all this stuff. Yes, it’s cool. It’s good and we can have estimates and try to hit them. Yes, I believe all that. But to purely try to quantify things like I’ve seen people try to do, it doesn’t work in a way that you wanted to, and it backfires, and you’re going to lose your best developers. If you want to build A+ or A software, you need really good developers and you need to treat it like a craft.
If you want to build C- or D+ software, then that’s fine treat it like manufacturing. It really is this thought of how we can not treat every department as if it were an MBA, that we got a degree and we think we can middle manage all the departments because software development is not the same as customer support.
Those are my thoughts for today. You might think of them as if I was blogging. That would have been the last six months of blog posts and instead of condensed them into audio format, hopefully, you get some nuggets of wisdom out of these thoughts that I’ve been having over the past several months.
I’ll be back next Tuesday morning with another episode of Startups for the Rest of Us. As always, if you have thoughts or feedback, you can head up to startupsfortherestofus.com. Post a comment on each episode. I read all the comments or you can tweet me at @robwalling. Thank you for listening this week. I’ll see you next time.
Episode 478 | A Few Things I Learned in 2019

Show Notes
In this episode of Startups For The Rest Of Us, Rob reflects back on his goals of 2019 and shares some lessons that are broadly applicable to founders/entrepreneurs. He also shares how he “unplugged” from the internet/devices while on a recent vacation with his family and the benefits he experienced.
Items mentioned in this episode:
I’m going to cover a couple of things today. I want to talk a little bit about unplugging, based on recent experience that I had going to the Dominican Republic with my family. It was my first time there. I unplugged, we unplugged for half of the trip. It was four days with no wifi and no Internet at all. I want to talk a little bit about that experience and the impact that it had on me, something that I want to make a habit of in this coming year.
I also want to revisit my 2019 goals. I know often around this time of the year, Mike and I revisit our prior year goals and we look ahead at the next year’s. I’m not going to do something nearly so formal, but I did want to talk through quickly, some of the goals that I had set for 2019. I have some other reflections on 2019, some lessons that I learned, that I think are pretty broadly applicable to founders and people doing hard things, ambitious folks trying to build something that is difficult.
If nothing else, I hope that you leave this episode with a sense that we’re all going through the same thing, we all experience these same thoughts, and experiences are very similar ones as we do these. It’s this feeling of, “Wow, I’m not moving fast as I want,” or, “I’m not very good at this,” or, “This is scary and I don’t really want to do this anymore. How am I going to fix this?” that type of thing. As I reflected back on stuff that’s happened over the past 12 months, it has been an absolute whirlwind. I want to talk through some of that today.
To start, over Christmas and New Years, I spent eight days in the Dominican Republic with my family. As I said, I had bever been, my kids had never been, but Sherry had, either spoken in an event or been in a retreat there earlier last year. She booked eight days for us and the later half of that was completely off the grid.
It was scary at first. I will admit. It’s weird, I’m not on Twitter and Facebook all the time, and I’m not in Slack all the time. I don’t need that constant dopamine rush of an app giving me feedback. It’s just not how I’m built. I shouldn’t say that’s not how I’m built because I have been there at times, but I’ve been very deliberate about not allowing myself to fall into that trap. Yet, I found myself frequently thinking of something, wanting to just know the answer right then, and wanting to Google it. Realizing, “Oh, I want to listen to that book,” going to Audible and not being able to download it. It was this slow grind on me, this realization of how reliant I am on external inputs.
I’ve always consumed a lot of media, typically reading books, listening to books, listening to podcasts. I do that because it gives me new ideas and fresh perspectives that allows me to view my day-to-day job in a different way, but it also allows me to come on this show and not say the same things over and over, to have an evolving perspective.
What I also realized is if anything, I consume a bit too much. Even though I feel I have a pretty good balance of consumption in production, in producing things, podcasts, conferences, accelerator or whatever, I realized during this four-day Internet fast that my mind wandered in glorious ways. I got so deep into topics that I just wouldn’t have stumbled upon, how I not had this time.
This wasn’t a retreat. I’d like to take a retreat once a year, maybe twice a year if I really need it. Typically, it’s a once a year cadence where I ask questions, then I sit down and write stuff. This was and that. I was with the family, I was not asking specific questions, I was really casually moving from one topic to the next, and it led to some real ground breaking insights, to some problems, or just issues that MicroConf expansion over the next 12-18 months, has a lot of logistics and a lot of things that we’re thinking about. How can we do this well? How can we make this better? I just had a lot of thoughts on it that didn’t have the space to come out in my day-to-day and creative ideas bring seemingly from nowhere, but they weren’t from nowhere. It’s all the thinking, the note taking, and just the 10,000 hours of going through this process. I think it was a real reminder for me to do this more often.
As I said, I only want to do a retreat every year or so. I actually think I want to do this off the grid thing quarterly. I feel like I could do it once a month, in all honesty. It was calming and soothing to just go away, turn off the Internet, and think about things. You can tell it rock my world, so that’s something that I want to try to do in 2020, is do this off the grid.
Bill Gates used to call it “think weeks” and I think he only did it once a year, but I wouldn’t necessarily go out with the intent of reading a bunch of books and synthesizing information. It really is, what are the broader issues at hand that I want to think about, but it’s also just let your mind wander almost in a meditative state, let the issues show themselves, let the thought show themselves, and let these creative insights come. That was a bigger realization for me.
If you already do that, I’m impressed. If you have never done this, obviously, it’s easier said than done given how busy all of our schedules are. It was pretty eye-opening to me, it is something that I believe is a practice that I am lacking in and I want to do better. That was unplugging.
Second topic I want to cover are goals that I had set for 2019. Really, I had four goals that I had set about. The first was exercise two or three times a week. I mostly achieved that. I was way ahead of it for a while. Once winter came, travel got in the way. I have absolutely fallen off the wagon. I feel that’s mostly a thumbs up-ish for me and it’s something that I need to keep doing especially as I get older. My birthday was just five day ago, so I’m another year older and I need to keep thinking about it.
I hate exercise. I just don’t want it. I never liked it. I was always an athlete in highschool and college, so I didn’t need to exercise, because that’s just what I did. It was built into this routine of, you go in your practice for two hours and you’re in this amazing shape, but that where I’m at. I have to set this goal for myself, otherwise, I don’t do it. That was number one.
Second one was to continue pushing TinySeed forward. It was to get the first batch chosen. It was to get the first batch to have a noticeable impact on their growth and not just me, obviously, but the program itself, the mentors. To make TinySeed essentially the preeminent accelerator for bootstrapper and for folks who don’t want to shoot the moon and who want to build this ambitious yet sane stuff for startups. I feel like that is on, or ahead of schedule with everything that I had envisioned and spoken with my co-founder, Einar. That feels like a win to me.
At this point, things are continuing to roll and frankly accelerating, both with TinySeed and the applications for batch two. We had a lot more folks with revenue, we had a lot more folks with tractions in the second application process. With MicroConf expansion, the way the podcast has continued, even though Mike has taken a step back, a lot of things are hitting on all cylinders. It hasn’t been easy and I’ll get into that a little later in this episode, but in taking stock on what happened in 2019, I’m pinching myself a little bit.
It’s interesting. I got an email last night actually and it was from Squarespace. It said, “Hey, your website, tinyseed.com is about to renew on the annual plan.” I emailed Einar and I said, “It was only a year ago that we started our first application process and that we had a website.” Before that, we did a landing page or something for a couple of months prior, but that’s it. It feels like it’s been two or three years based on how fast things have moved and how ambitious we’ve been with it, but how things have come together.
Not everything comes together, that’s for sure, but there was so much work to be done when this Squarespace site went live and we started taking applications. It’s that sense of we didn’t have a bunch of systems in place. We didn’t have much of employees. We didn’t have a bunch of funding. It was the two of us and we are raising enough money to trying to do the first batch. We didn’t have an amazing application process. It was a Google form that fed into a Google Sheet, that when people ask, “Hey, I’d love to get a confirmation email.” I sat and thought, am I going to write some code to make it to this? Am I going to have to go back and hack PHP, or learn Ruby to make it do this?
Of course, I remembered Zapier monitoring Google Doc and say, “That was it, it was just gum and bailing wire, and you’re just trying to keep it together,” but the outward appearance was not that. The fact that I was sifting through 880 something rows in a Google Sheet, trying to sort things, interview people, and doing 70 something calls, it’s the image of that duck that’s on the water. From above, it looks calm, but underneath you’re just paddling like crazy. This is as much as startup is as anything I’ve ever done in terms of the uncertainty and just the scrappiness that you have to do.
In that startup life, I used to work with a guy who would say, “In startup world, a week is a month, a month is a quarter, a quarter is like a year, because you’re moving so fast.” That’s been a big reflection of me. I think something I’m pleased about with 2019 is, I don’t work a ton of hours. I don’t work 50-hour weeks. I work normal work weeks. I take time off to reflect, and I feel like that.
My advice to you if you’re not already thinking this way is that’s how you play long ball. That’s how you do this for 15 or 20 years because being an entrepreneur is very, very hard. As we know, it’s extremely stressful. If you work this 50–60 hour weeks, you can do it for a short period of time, but over time, it degrades your ability to produce. Anyway, that’s the reflection on TinySeed. I’m going to talk a little bit more about MicroConf in the podcast in a couple of minutes.
My third goal was to not not freak out when the stock market crashed in 2019. That just didn’t it happen. That was more of a prediction than anything. I’m not sure if that was actually a goal.
The last goal that I completely failed on was to write, or re-write a book. That one has been on my list for years and it’s always been a Plan B, that if I have time, I really want to re-write Start Small, Stay Small. I still get a lot of emails about it. It’s still 90% applicable, but it’s dated. Some of the links don’t work and there’s just certain tactics that don’t work. I’m at the point where I kind of throw my hands up, like is this something I think I can pull off in the next year? I just don’t know. I need to get more thoughts to doing that.
The interesting thing for me is my day-to-day work, not my personal life, but work life has really come down to three things: MicroConf, this podcast, and TinySeed. I’ve already talked a bit about TinySeed and what we did last year. A question I get (actually often) is, “How do you get so much done or how do you run all three of these things? They seemed very time consuming.” It’s often hard. I’ll answer, “Well, I have a Trello board and I have a process, all these and all that,” and that’s part of it, being efficient, being fast with email, and delegating all these stuff.
I think the biggest thing that has saved me hundreds of hours, if not thousands, is this division of responsibilities to extremely capable people. It didn’t happen by accident, but it’s something that I’ve learned over the years. Some people get here really quickly. Some people immediately think, “I need senior project thinkers who can get things done.”
I started with a very limited budget because I was a bootstrapper, with basically no budget and a salary for my day job. I went for a work week route in 2007 and started hiring VAs, which are very task-based people. You need heavy process. That worked for that stage, so I hung on to that stage too long, that stage of task-based people.
That was really right before Drip and it wasn’t until Drip where I realized, “Wow, hiring project people, where they can handle an entire project, even if they need some training, they’re more expensive than task based, but they’re such a step-up in terms of how much you can delegate, much you can give and expect results.”
I think the next step up is a product person. Someone who isn’t just working on a project and managing that in timelines and dates because you can find a lot of project managers, but how many product people can you find? By product, I don’t mean software, I mean a podcast, if you think about it, is a product. A producer could produce it in a way that’s really at a high level. That’s better than someone who, you’re just like, “Okay, these are the dates and these are the timelines of the podcast. This is who needs to be on.”I was actually thinking about how do I make this better, how do I think ahead and add things to this.
The same thing with your software product that you’re managing. Obviously, it’s a product. The same thing with MicroConf. That’s a product if you think about it. It’s a bunch of different smaller events. Now, it’s online stuff. It’s the state of indie SaaS report and the live video stream that’s going to come along with it, the Slack channel and all of that. It’s all really product-based thinking.
While I could sit down with someone and outline, “Hey, week-to-week, month-to-month, this is what needs to happen and someone could logistically do it.” How do you find someone who’s one layer above that? As a product thinker, something with TinySeed as an accelerator. It’s a bit of a luxury, but it’s a realization I’ve had that there is no chance that MicroConf, TinySeed, and the podcast could all exist at the level that it does, without many product-based thinkers.
That started off as Einar and myself, and then Tracy joined the team to be thinking about TinySeed. It’s not just how do we run TinySeed, but it’s how do we make it better constantly and new suggestions of how do we improve this process. I talked about our application process for batch one, that was bailing wire and duct tape. When the second one came around, Tracy evaluated all these tools, just went off, and made recommendations to us. Basically made a decision to make this thing better and more manageable. It is, it’s better. We look at it as v2.0 of our whole process.
As we expand, because we’re going to fund more companies with this second batch than we did in the first, obviously, batch three, four, five will expand from there. These things have to get better. I think that the scrappiness of that initial one of just getting it done is what a lot of us founders are really good at. How can you find a person if you’re not good, I’m not great at, then putting that into writing, communicating a process, and improving upon that process constantly iterating, that’s not my strong suit. But that’s okay because you can find people, you can hire people, you can work with people who can help you with that. That’s where you’re really going to level up, is where you figure out your strengths. You double down on those and how do you backfill against your weaknesses.
Speaking of the podcast, I have to admit, I haven’t talked about this on the show. With episode 448, when Mike and I had a really intense conversation about him stepping back, focusing on Bluetick, and whether or not he should, that whole thing (again, if you haven’t listened to that) is one of the best episodes of this entire (almost) 500 episode run, in my opinion.
I was kind of scared after that because how do you take something that has been running for close to 10 years with two people, has a very defined format, we have not iterated very much on the format, and how do you reinvent it in a way that hopefully: (a) isn’t the worst, (b) isn’t just as good but is actually better, how do you do that? That’s a task that I was faced with back in that May–June time frame. It’s close to seven months now.
I’ve done some experiments. I’ve tried different show formats, Q&A with different people. Obviously, have been doing interviews but trying to do interviews in a different way than everyone else does, hot seats, there are some solo episodes like this, but there was a lot of uncertainty there for me. I certainly felt more trepidation and angst about keeping it going and I how I would do that. I was also highly motivated.
There’s this interesting thing growing up. It was not an option for me and my siblings to quit things. I don’t want to sound like the old guy who walked uphill both ways in the snow, which I did not do (I rode a bus to school), but being in school, I was one of the scholar athletes where I got straight As and also played two sports. It was just a given, that I got on the bus at 7:30 and my parents pick me up after football practice at 7:00 or 7:30. It was just 12-hour days and I never once thought this is hard, I shouldn’t do this. It was just, this is what we do as scholar athletes or as entrepreneurs. We do the hard things. I think it’s almost easier when you don’t question them. There was, of course, a certain point you can drive yourself to depression, there’s health issues, there’s a bunch of stuff.
When Mike took a step back, I never once thought, “Well, I guess we should shut the show down. I guess we should end the podcast,” because it’s just not an option to quit. Again, there are exceptions. It’s an option to quit if your startup isn’t working, you’re going bankrupt. There are things, there are ways, but in these scenarios where it’s not everything falling off a cliff, but it’s like this is hard, or this is a mental challenge, or a physical challenge, for that matter, which is what it was growing up in highschool and college. It was hard workouts, it was staying up then to try to finish homework, it was being tired a lot, that kind of stuff. Again, it’s just wasn’t an option not to do it. I think that’s a skill. That skill of hard work and the ability to not just question things, I think has served me well.
The feedback I’ve gotten on the new podcast format has been overwhelmingly positive. I’ve loved the constructive feedback I have received and I’m making tweaks to the show format, the week-to-week stuff. I plan on once again continue to double down on the show in 2020. My love that I have, the freedom to experiment with things, and sometimes they work and sometimes they don’t. I love that I have the time to do it.
I know I have a limited time, given everything else, but it is in line with MicroConf and even with TinySeed, the ability to do TinySeed Tales. I wanted to do TinySeed Tales for five years, that high level of NPR production. Didn’t have the time, didn’t have the budget, and this moment is essentially was an excuse for me to do that. We are certainly looking at a season two of TinySeed Tales. Plan to keep doing that based on the feedback I received.
One more reflection on 2019 I wanted to share with you before I wrap is once again that reinforcement, that running something on autopilot or doing something for the second, third, fourth, fifth time is not that hard. But launching new things is extremely time consuming in way more than you think it’s going to be. This is the reason why I always advise people who say, “Hey, I’m going to try to launch or grow two pruducts at the same time, even two info products,” to don’t do that. Grow one, get it to a plateau, auto-pilot it as much as you can, and focus on the other, because launching two things is time consuming, it’s mentally taxing.
With MicroConf, we’ve done 19 of them, our 20th, and our 21st are here in a couple of months. We’re pretty good at them at this point. Obviously, we can always improve, but it’s not a decision point of everything of what should the format be? What should the meals be? What should the schedule be? Really, it’s a known quantity. Even if we revamp it and tweak it each year, that’s a known quantity. It isn’t as time-consuming as something that you think is going to be pretty quick. Like the example that I’m experiencing, that I just spent five hours yesterday working on, is a state of independent SaaS survey and report. I literally thought that I could hire a designer, hire a statistician, then draft a survey, and hand most of it off to be done. That has not been the case.
We are literally hundreds, hundreds of person hours into this, including the designer statistician and my time. It has been so much more of my time than I estimated or anticipated. It’s worth it. Like the results, I’m starting to see we have versions of the report now that we’re tweaking and it’s absolutely worth every minute and every dollar that we’re spending on it. But it is that reminder to me that everything is new, everything is a decision, and everything has to be thought through from square one, about how we word things, the look, the feel, how we analyze, and what assumptions we’re making. It’s just that everything is new.
That’s the same thing when you’re building a product. You don’t know what features to build next, what customer to listen to, and everything is new. You don’t know if your pricing is off, you don’t know if your messaging is off, you don’t know if your positioning is off, you don’t know if your brand is off, or all of those things is on and only one os off. It’s just so hard, there’s so many variables, so many decisions to make. This is why launching new things is time consuming, it’s mentally taxing, and it really takes a founder mentality to do it.
You can’t hand off a task that requires a founder to a project person, or oftentimes, even a really good product person has a tough time doing something from scratch. There’s this very unique skill set that takes something from zero to one, in that sense, from zero to existence. It’s really hard. I do believe it’s something that we get better at the more you do. I also think that it’s one of the hardest things that I’ve done over and over.
There’s this old marketing adage, you launch a new product to an existing audience or existing products to a new audience, but never do both at once. That means a new product to a new audience. Frankly, at some point in your career, you have to, because nobody starts out without an audience or a product and that is the hardest part. As you’re grinding it out, as you’re struggling through these decisions, the uncertainty of what you’re doing, rethinking your pricing and thinking, “Wow, everyone else has this figured out, why don’t I know what to do? Why don’t I know the right answer?” The answer is, no one else really does either.
In closing, I’m not sure if there has been a year in recent memory that I have looked forward to more than 2020. For me, personally, it’s a lot of friends. I’m enjoying the podcast, loving, doubling down on that. I’m loving the way that TinySeed is expanding and I’m super stoked, honestly, about MicroConf in the expansion. It’s just everything that I’ve been working on for 15 years has come together in a way that I don’t think I could have imagined. It makes the hard days and the set backs so much easier to fight through when you have the winds along the way and when you have good people, talented people that you really enjoy working with, and that essentially you’re constantly collaborating with to make whatever it is that you’re working on better.
With that, I’ll wrap up this episode, I wish you a prosperous, a successful, and a happy 2020. Thank you so much for being a listener of Startups for the Rest of Us for all these years. In a couple of months, we’re going to be at our 500th episode, 10 years, and it comes even before that point. It’s just a pleasure to be able to get on the mic and talk to you every week.
Thank you so much for listening. Thank you for all your support, your feedback, and your comments. I’ll see you next time.